Your step (4) to me appears to be wrong.  If you are to install openssl to the 
following directory:

                C:\Program Files (x86)\OpenSSL\

then you need to do:

?  perl Configure VC-WIN32 -prefix=C:\Program Files (x86)\OpenSSL

When I build openSSL I use nasm, so after the above I do:

?  ms\do_nasm

?  nmake -a -f ms\nt.mak

?  nmake -f ms\nt.mak test

?  nmake -f ms\nt.mak install

Does that help at all?

From: openssl-users [] On Behalf Of 
Jing Liu
Sent: 21 September 2016 13:35
Subject: [openssl-users] Failed to install OpenSSL 1.1.0 using 'nmake install'

I've tried all my best to solve this problem but failed. Can you help me?

- OS: Windows 10
- Perl: ActivePerl 5.12.2 build 1202
- Development environment: MS Visual Studio 2010 SP1
- OpenSSL version: OpenSSL 1.1.0

I tried to compile and install OpenSSL 1.1.0 according to the following steps:

1. decompressed OpenSSL 1.1.0 software package to directory "D:\openssl-1.1.0";
2. opened the "Visual Studio 2010 command prompt" window using an Administrator 
3. switched to the directory "D:\openssl-1.1.0";
4. D:\openssl-1.1.0> perl Configure VC-WIN32;
5. D:\openssl-1.1.0> nmake;
6. D:\openssl-1.1.0> nmake test;

> So far, all steps went smoothly, but ...

7. D:\openssl-1.1.0> nmake install;

Here, I got the following error and there was no file being copied to the 
destination directories even though those directories were successfully created.

    Microsoft (R) program maintenance utility 10.00.30319.01 copy right (C) 
Microsoft Corporation.All rights reserved.
*** Installing development files
created directory 'C:/Program Files (x86)/OpenSSL'
created directory 'C:/Program Files (x86)/OpenSSL/include'
created directory 'C:/Program Files (x86)/OpenSSL/include/openssl'
Can't Open "./ms/applink.c" at .\util\ line 61.
NMAKE : fatal error U1077: "C:\Perl\bin\perl.exe": return code "0x16"

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